Nitrogen → [4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-methanol

HRID 1446745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446745
N#N.[Cl:3][C:4]1[CH:9]=[CH:8][N:7]2[C:10](I)=[CH:11][N:12]=[C:6]2[CH:5]=1.[OH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>>[Cl:3][C:4]1[CH:9]=[CH:8][N:7]2[C:10]([C:19]3[CH:20]=[CH:21][C:16]([CH2:15][OH:14])=[CH:17][CH:18]=3)=[CH:11][N:12]=[C:6]2[CH:5]=1

Komponenten

5

Edukt 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 574976977-Chloro-3-iodoimidazo[1,2-a]pyridine

Produkt 1

HCID 68544639[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-methanol

Versuchsvorschrift

Charge a 50 mL round bottom flask equipped with: a magnetic stirrer, temperature controlled heating mantle, N2 atmosphere, condenser, with 7-chloro-3-iodo-imidazo[1,2-a]pyridine (1.0 g, 3.6 mmol), 4-(hydroxymethyl)phenyl boronic acid (570 mg, 3.75 mmol), 2 M K2CO3 (7 mL), dimethoxy ethane DME (25 mL). Deoxygenate with a nitrogen purge and add Pd(TPP)4 (200 mg, 0.17 mmol 5 mol %) and heat the reaction to 65° C. for 48 hours. Cool the reaction and siphon off the lower aqueous phase (5 mL). Evaporate the reaction under vacuum at 42° C. to remove DME. Take up the residue in CH2Cl2 and wash with water (15 mL). Concentrate the CH2Cl2 and chromatograph giving an oil that solidified on standing to an ivory solid 670 mg (72%) MS (ES), m/z 259.1 (M+1).

Aufarbeitung

  1. additionCharge a 50 mL round bottom flask
  2. customequipped with: a magnetic stirrer
  3. customDeoxygenate with a nitrogen
  4. custompurge
  5. temperatureheat
  6. customthe reaction to 65° C. for 48 hours
  7. temperatureCool
  8. customEvaporate
  9. customthe reaction under vacuum at 42° C.
  10. customto remove DME
  11. washwash with water (15 mL)
  12. concentrationConcentrate the CH2Cl2 and chromatograph
  13. customgiving an oil that

Quellen und Nachweise

ORD-Eintrag
ord-03ad6ad1ff6d4f3294f5ec974c90954b
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666879B2

Notizen zur Reaktion

Wird geladen…